Activatable Near-Infrared Fluorescence Imaging Using PEGylated Bacteriochlorin-Based Chlorin and BODIPY-Dyads as Probes for Detecting Cancer

• Published in: Bioconjugate chemistry Vol. 30; no. 1; pp. 169 - 183
• Main Authors: Ogata, Fusa, Nagaya, Tadanobu, Maruoka, Yasuhiro, Akhigbe, Joshua, Meares, Adam, Lucero, Melissa Y, Satraitis, Andrius, Fujimura, Daiki, Okada, Ryuhei, Inagaki, Fuyuki, Choyke, Peter L, Ptaszek, Marcin, Kobayashi, Hisataka
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 16.01.2019; Amer Chemical Soc
• Subjects: Animals; Antibodies, Monoclonal - chemistry; Biochemical Research Methods; Biochemistry & Molecular Biology; Biomedical materials; Boron; Boron Compounds - chemistry; Cancer; Cell Line, Tumor; Chemical compounds; Chemistry; Chemistry, Multidisciplinary; Chemistry, Organic; Conjugation; Fluorescence; Fluorescent Dyes - chemistry; Fluorescent indicators; Fluorophores; Heterografts; Humans; Infrared imaging; Life Sciences & Biomedicine; Mice; Neoplasms - diagnostic imaging; Optical Imaging - methods; Peptides; Pharmacokinetics; Pharmacology; Physical Sciences; Polyethylene glycol; Polyethylene Glycols - chemistry; Porphyrins - chemistry; Probes; Science & Technology; AGENT; SURGERY; IMPROVE; FLUOROPHORES; PERFORMANCE; CONJUGATE; OVARIAN-CANCER; ABSORPTION; EMISSION; ENERGY-TRANSFER ARRAYS
• ISSN: 1043-1802; 1520-4812
• DOI: 10.1021/acs.bioconjchem.8b00820

Near infrared (NIR) fluorescent probes are attractive tools for biomedical in vivo imaging due to the relatively deeper tissue penetration and lower background autofluorescence. Activatable probes are turned on only after binding to their target, further improving target to background ratios. However, the number of available activatable NIR probes is limited. In this study, we introduce two types of activatable NIR fluorophores derived from bacteriochlorin: chlorin–bacteriochlorin energy-transfer dyads and boron-dipyrromethene (BODIPY)-bacteriochlorin energy-transfer dyads. These fluorophores are characterized by multiple narrow excitation bands with relatively strong emission in the NIR. Targeted bacteriochlorin-based antibody or peptide probes have been previously limited by aggregation after conjugation. Polyethylene glycol (PEG) chains were added to improve the hydrophilicity without altering pharmacokinetics of the targeting moieties. These PEGylated bacteriochlorin-based activatable fluorophores have potential as targeted activatable, multicolor NIR fluorescent probes for in vivo applications.